As a long time FI I have witnessed people getting the own airplane virus.
Bothered by dirty rental planes with small technical issues, non-availability, they start with a search for a C172 or the likes. And ask me for advice.
I tell them the spectrum is between a Piper Cub and a private B747-400, all with their pro and cons. What the bigger and faster one brings, You loose from a simpler one.
After discovering an own plane costs a lot of money and brings worries, eats up precious time, most stop at this level.
But for some, due to the availability of resources (enough money...), it keeps on going and after the prop twin or SE Turbine they end up with twin jets.
For some that route is quite fast, faster than one would consider as smart. (no so long a go one P51 owner crashed fatally with his plane, it turned out he started flying less than one year before...).
I like to state that almost all people I know that arrive to the point that they can afford an expensive jet, are hard working people. If that hard work brings also a good financial state, it brings also the worries and time needed for a fleet of cars, a mansion and one or more weekend houses. Apart from the familiy life, all eat up time.
Getting from nil to the level of a SP flown jet will cost a huge amount of time and resources, and it never stops.
Most business plane owners have discovered that flying a complex jets does not mix with a business meeting and hire at least an experienced safety pilot, or better, a professional crew to at least do the dirty work before the flight.
Pure private pilots that cannot subtract crew cost from their private tax income, tend to bypass this. What is more rewarding if You as the head of the family can offer the luxury of flying them almost anywhere, anytime.
To be honest, my thoughts are with that family and the pilot. He wished and did the best for his family, but it turned into a dramatic outcome.
On the other hand, with 18000 safe airline hours, well trained with expert other crew members: flying single pilot in a fast twin jet with low type hours, in a dark night with all kinds of weather phenomena, is not even LOW on my bucket list, I would pass that one on.